2-Methylpiperidine → HCID 24981321, compound

HRID 533720Notes

Reaction equation

HRID 533720 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.N=C=N.[CH:23]1[CH:24]=[CH:25][C:26]2N(O)N=[N:29][C:27]=2[CH:28]=1.CCN(C(C)C)C(C)C.CC1CCCCN1.C(=O)([O-])[O-]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:10])[C:11]2[CH:12]=[CH:13][C:14]([C:15]([N:29]3[CH2:25][CH2:24][CH2:23][CH2:28][CH:27]3[CH3:26])=[O:17])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1

Participants

9

Reactant 6

HCID 79742-MethylpiperidineHCID 19660Carbonate IonHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 160435CarbodiimideHCID 12092493HCID 12092493, compound

Product 1

HCID 24981321HCID 24981321, compoundYield 383.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(4-fluorophenylcarbamoyl)benzoic acid (50 mg, 0.19 mmol) in DMF (1 mL) was added PS-Carbodiimide (125 mg, 0.25 mmol), HOBt (26 mg, 0.19 mmol), DIPEA (52 mg, 0.40 mmol) and 2-methylpiperidine (25 mg, 0.25 mmol). The reaction was agitated at room temperature for 18 h. To the reaction was added MP-carbonate and agitated for a further 8 h. The reaction was filtered and concentrated under vacuum to afford diluted with water (10 mL) and isolated the white precipitate by vacuum filtration to afford N-(4-fluorophenyl)-4-(2-methylpiperidine-1-carbonyl)benzamide (248 mg, 95%). 1H-nmr (400 MHz, d6-DMSO) δ 10.37 (br s, 1H), 8.00 (d, J=7 Hz, 2H), 7.83-7.72 (m, 2H), 7.49 (d, J=7 Hz, 2H), 7.21 (t, J=8 Hz, 2H), 3.52-3.01 (m, 3H), 1.75-1.29 (m, 6H), 1.21 (m, 3H); MS (ESI) m/z 341.4.

Workup

  1. stirringagitated for a further 8 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated under vacuum
  4. customto afford
  5. customisolated the white precipitate
  6. filtrationby vacuum filtration

Sources & evidence

ORD record
ord-da1b2751822b4a2d96c878ddb891e75c
Source dataset
uspto-grants-2014_10
Patent number
US08853392B2

Reaction notes

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